methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside | 131000-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(formyloxymethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 131000-31-2
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: UERYMPDJAFWNGO-RGDJUOJXSA-N

物化性质

• 熔点：
  89-90 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  402.0±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside 以 甲醇 为溶剂， 反应 72.0h， 以60%的产率得到甲基2,3,6-三-O-乙酰基吡喃己糖苷
  参考文献：
  名称：

  Formylation of primary hydroxyl groups in sugars

  摘要：

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.

  DOI：

  10.1016/0008-6215(90)84006-g
• 作为产物：
  描述：

  methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 25.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-formyl-α-D-glucopyranoside
  参考文献：
  名称：

  A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters

  摘要：

  A convenient method has been developed for a facile and high-yield conversion of 6-O-tertbutyldimethylsilyl and 6-O-trityl protected monosaccharides to their formate esters, which may serve as useful intermediates for the replacement of the primary hydroxyl group of sugars by other functional groups.

  DOI：

  10.1080/07328300600859668

文献信息

• Biomimetic Seleninates and Selenonates
  作者：Mohannad Abdo、Spencer Knapp

  DOI：10.1021/ja8034448

  日期：2008.7.1

  The synthesis of a variety of pyranose-, nucleoside-, (amino acid)-, and polyhydric-based seleninic and selenonic acids by DMDO oxidation of the corresponding selenoesters is reported, as well as some unusual coupling reactions of the seleninate and selenonate functionality with biological nucleophilic groups (sulfhydryl, indole, phenol, imidazole, carboxamide) that are found in proteins and enzyme

  据报道，通过 DMDO 氧化相应的硒酸酯，合成了各种吡喃糖、核苷、（氨基酸）和多羟基硒酸和硒酸，以及硒酸和硒酸官能团与在蛋白质和酶活性位点中发现的生物亲核基团（巯基、吲哚、苯酚、咪唑、甲酰胺）。
• Selective Synthesis Under Microwave Irradiation of Carbohydrate Derivatives Containing Unsaturated Systems
  作者：Marta M. Andrade、Maria Teresa Barros、Paula Rodrigues

  DOI：10.1002/ejoc.200700154

  日期：2007.8

  The selective synthesis of sugars containing vinyl ester- and vinyl ether-type side chains was developed by means of esterification and Wittig olefination procedures. The studies were focused on the anomeric position of D-xylose and on the primary carbon positions of D-glucose and sucrose. Microwave heating was used in both cases, and the results obtained show the usefulness of microwave irradiation

  含有乙烯基酯和乙烯基醚型侧链的糖的选择性合成是通过酯化和 Wittig 烯化程序开发的。研究集中在 D-木糖的异头位置以及 D-葡萄糖和蔗糖的主要碳位置。在这两种情况下都使用了微波加热，所获得的结果表明微波辐射对于开发碳水化合物化学清洁技术的有用性。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Facile conversion of O-silyl protected sugars into their corresponding formates using POCl3·DMF complex
  作者：Marta M. Andrade、M. Teresa Barros

  DOI：10.1016/j.tet.2004.07.056

  日期：2004.10

  The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex (POCl3DMF)-D-. was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue. (C) 2004 Elsevier Ltd. All rights reserved.
• GAN, LI-XIAN;WHISTLER, ROY L., CARBOHYDR. RES., 206,(1990) N, C. 65-69
  作者：GAN, LI-XIAN、WHISTLER, ROY L.

  DOI：——

  日期：——